Acetic Anhydride → 1-Acetyl-6-aminoindoline

HRID 1870900Notes

Reaction equation

HRID 1870900 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)C.[Pd]>[C:13]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=2)[CH2:8][CH2:9]1)(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 297576-Nitroindoline

Product 1

HCID 2585641-Acetyl-6-aminoindolineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Nitroindoline (15.63 g, 0.095 mol) was refluxed for 0.25 h in acetic anhydride (100 ml), cooled, and the precipitate filtered and washed with water, before drying in vacuo. This material (16.6 g, 0.08 mol) was hydrogenated in ethanol (500 ml) over 10% palladium on charcoal (3.4 g of 50% paste in water). The catalyst was removed by filtration and the filtrate was evaporated to leave the title compound as an off-white/cream powder (12.59 g; 89%).

Workup

  1. temperaturecooled
  2. filtrationthe precipitate filtered
  3. washwashed with water
  4. custombefore drying in vacuo
  5. customThe catalyst was removed by filtration
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-916f188cad4344939d671a509522832e
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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